1-(2-azidophenyl)-2-(tert-butylamino)-2-oxoethyl acetate | 1193490-24-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(2-azidophenyl)-2-(tert-butylamino)-2-oxoethyl acetate
• 英文别名: [1-(2-Azidophenyl)-2-(tert-butylamino)-2-oxoethyl] acetate；[1-(2-azidophenyl)-2-(tert-butylamino)-2-oxoethyl] acetate
• CAS: 1193490-24-2
• 化学式: C₁₄H₁₈N₄O₃
• 分子量: 290.322
• InChiKey: SSOFVCAVPLCAEZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  69.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(2-azidophenyl)-2-(tert-butylamino)-2-oxoethyl acetate 在 三苯基膦 作用下， 以 甲苯 为溶剂， 反应 5.0h， 以80%的产率得到N-(tert-butyl)-2-methyl-4H-3,1-benzoxazine-4-carboxamide
  参考文献：
  名称：

  New efficient synthesis of 4-aminocarbonyl substituted 4H-3,1-benzoxazines by a Passerini 3CC/Staudinger/aza-Wittig sequence

  摘要：

  alpha-Acyloxy-carboxamide azides 1, obtained from Passerini reaction of easily accessible o-azidobenzaldehyde with isocyanides and carboxylic acids, reacted with triphenylphosphine to give various 4-aminocarbonyl substituted 4H-1,3-benzoxazines 3 in moderate to high yields via sequential Staudinger and intramolecular aza-Wittig reaction. However, alpha-hydroxy carboxamide azides 5 were obtained in moderate yields when pyruvic acid was used in the Passerini reaction. Further sequential reaction of azides 5 with triphenylphosphine and isocyanates produced 2-amino-4-aminocarbonyl substituted 4H-1,3-benzoxazines 8 via a tandem Staudinger/aza-Wittig/heterocumulene-mediated annulation. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.08.022
• 作为产物：
  描述：

  2-azidobenzyl alcohol 在 2,2,6,6-四甲基哌啶氧化物 、 碘苯二乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 49.0h， 生成 1-(2-azidophenyl)-2-(tert-butylamino)-2-oxoethyl acetate
  参考文献：
  名称：

  OPHA（氧化-Passerini-水解-烷基化）策略：烷基化Passerini反应的四步单罐改进

  摘要：

  如果与多步有机合成方法进行比较，通常会认识到多组分反应的效率和收敛性。尽管如此，我们在这里证明了四步一锅法（即涉及到的四个步骤的初始命名为OPHA策略）不仅能够提供无法通过烷基化的Passerini反应获得的化合物，而且还能够产生与典型的多组分方法一样，它们具有最小的原子损失和高度的操作简便性。

  DOI：

  10.1021/ol500813p

文献信息

• New efficient synthesis of 4-aminocarbonyl substituted 4H-3,1-benzoxazines by a Passerini 3CC/Staudinger/aza-Wittig sequence
  作者：Ping He、Jing Wu、Yi-Bo Nie、Ming-Wu Ding

  DOI：10.1016/j.tet.2009.08.022

  日期：2009.10

  alpha-Acyloxy-carboxamide azides 1, obtained from Passerini reaction of easily accessible o-azidobenzaldehyde with isocyanides and carboxylic acids, reacted with triphenylphosphine to give various 4-aminocarbonyl substituted 4H-1,3-benzoxazines 3 in moderate to high yields via sequential Staudinger and intramolecular aza-Wittig reaction. However, alpha-hydroxy carboxamide azides 5 were obtained in moderate yields when pyruvic acid was used in the Passerini reaction. Further sequential reaction of azides 5 with triphenylphosphine and isocyanates produced 2-amino-4-aminocarbonyl substituted 4H-1,3-benzoxazines 8 via a tandem Staudinger/aza-Wittig/heterocumulene-mediated annulation. (C) 2009 Elsevier Ltd. All rights reserved.
• OPHA (Oxidation–Passerini–Hydrolysis–Alkylation) Strategy: a Four-Step, One-Pot Improvement of the Alkylative Passerini Reaction
  作者：Fabio De Moliner、Martina Bigatti、Luca Banfi、Renata Riva、Andrea Basso

  DOI：10.1021/ol500813p

  日期：2014.4.18

  Multicomponent reactions are often recognized for their efficiency and convergency, if compared with multistep organic synthesis. Nevertheless, we here demonstrate that a four-step-one-pot approach (named OPHA strategy for the initials of the four steps involved) is not only able to afford compounds that could not be obtained by an alkylative Passerini reaction but also capable of generating them with

  如果与多步有机合成方法进行比较，通常会认识到多组分反应的效率和收敛性。尽管如此，我们在这里证明了四步一锅法（即涉及到的四个步骤的初始命名为OPHA策略）不仅能够提供无法通过烷基化的Passerini反应获得的化合物，而且还能够产生与典型的多组分方法一样，它们具有最小的原子损失和高度的操作简便性。